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Depends on the size of the hole and which tooth. If it is an upper molar, the roots could be within the sinus cavity. And when there is sinus pressure present, it could cause headaches on the same side. Also, if the hole on the tooth is large enough, air, hot and cold stimuli and food could set the nerve off, triggering a headache. You should see your dentist for futher x-rays and examination.

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Q: Could a hole in the tooth on the right side cause severe headaches on that side?
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